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5,5-Diphenylhydantoin

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Company Name: Henan DaKen Chemical CO.,LTD.
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Products Intro: Product Name:5,5-Diphenylhydantoin
CAS:57-41-0
Purity:99% Package:100g,500g,1KG,10KG,100KG
Company Name: Henan Tianfu Chemical Co.,Ltd.
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Products Intro: CAS:57-41-0
Purity:99% Package:500G;1KG;5KG;25KG
Company Name: Mainchem Co., Ltd.
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Products Intro: Product Name:5,5-Diphenylhydantoin
CAS:57-41-0
Company Name: PI & PI BIOTECH INC.
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Products Intro: Product Name:Phenytoin
CAS:57-41-0
Purity:90%+ Package:10mg, 25mg, 50mg, 100mg, Other scale please email Sales@pipitech.com Remarks:5,5-Diphenylimidazolidine-2,4-dione.
Company Name: Hubei Jusheng Technology Co.,Ltd.
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Products Intro: Product Name:phenytoin
CAS:57-41-0
Purity:99% Package:5KG;1KG Remarks:C15H12N2O2
5,5-Diphenylhydantoin Basic information
Description Generic formulation Indications Dose titration Plasma levels monitoring Cautions Interactions Special populations Behavioural and cognitive effects in patients with epilepsy Psychiatric use
Product Name:5,5-Diphenylhydantoin
Synonyms:PHENYTOIN BASE;PHENYTION;PHENYTOIN;5,5-DIPHENYLHYDANTHOIN;5,5-DIPHENYLHYDANTOIN;5,5-DIPHENYL-2,4-IMIDAZOLIDINEDIONE;DIPHENYLHYDANTOIN;LABOTEST-BB LT00159593
CAS:57-41-0
MF:C15H12N2O2
MW:252.27
EINECS:200-328-6
Product Categories:-;API's;Aromatics;Heterocycles;API intermediate
Mol File:57-41-0.mol
5,5-Diphenylhydantoin Structure
5,5-Diphenylhydantoin Chemical Properties
Melting point 293-295 °C(lit.)
Boiling point 395.45°C (rough estimate)
density 1.1562 (rough estimate)
refractive index 1.5906 (estimate)
Fp 11 °C
storage temp. 2-8°C
solubility DMSO: soluble
pkapKa 8.43(H2O,t =25,I=0.025) (Uncertain)
form Powder
color White to almost white
Water Solubility <0.01 g/100 mL at 19 ºC
Merck 14,7322
BRN 384532
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
InChIKeyCXOFVDLJLONNDW-UHFFFAOYSA-N
CAS DataBase Reference57-41-0(CAS DataBase Reference)
NIST Chemistry Reference5,5-Diphenylhydantoin(57-41-0)
EPA Substance Registry System2,4-Imidazolidinedione, 5,5-diphenyl-(57-41-0)
Safety Information
Hazard Codes T,Xn,F
Risk Statements 45-61-22-63-40-39/23/24/25-23/24/25-11-20/21/22
Safety Statements 53-45-36/37-16-7
RIDADR 2811
WGK Germany 3
RTECS MU1050000
Autoignition Temperature550 °C
HazardClass 6.1(b)
PackingGroup II
HS Code 29332100
Hazardous Substances Data57-41-0(Hazardous Substances Data)
ToxicityLD50 in mice (mg/kg): 92 i.v.; 110 s.c. (Stille, Brunckow)
MSDS Information
ProviderLanguage
5,5-Diphenyl-2,4-imidazolidinedione English
ACROS English
SigmaAldrich English
ALFA English
5,5-Diphenylhydantoin Usage And Synthesis
DescriptionPhenytoin is a first- generation antiepileptic drug (AED) known with the proprietary brand name of Epanutin® (Pfizer, Tadworth) in the UK and Dilantin® (Pfizer, New York, NY) in the USA.
Generic formulationMHRA/ CHM advice to minimize risk when switching patients with epilepsy between different manufacturers’ products (incl. generic products):
  • Doctors are advised to ensure that their patients are maintained on a specific manufacturer’s product.
IndicationsEpilepsy
Monotherapy and adjunctive therapy of focal and generalized tonic- clonic seizures.

Recommendations summarized from NICE (2012)
  • Seizure types: on referral to tertiary care (focal seizures), contraindicated (generalized tonic- clonic seizures if there are absence or myoclonic seizures or if juvenile myoclonic epilepsy is suspected, absence seizures, myoclonic seizures).
  • Epilepsy types: on referral to tertiary care (benign epilepsy with centrotemporal spikes, Panayiotopoulos syndrome, late- onset childhood occipital epilepsy), contraindicated (absence syndromes, juvenile myoclonic epilepsy, idiopathic generalized epilepsy, Dravet syndrome).
Dose titrationEpilepsy
150–300 mg od or divided into two doses, then increased to 200– 500 mg daily (dose to be increased gradually as necessary, with plasma phenytoin concentration monitoring).
Plasma levels monitoringPhenytoin has a narrow therapeutic index and the relationship between dose and plasma. Phenytoin concentration is non- linear: small dosage increases in some patients may produce large increases in plasma concentration with acute toxic adverse effects. Similarly, a few missed doses or a small change in phenytoin absorption may result in a marked change in plasma phenytoin concentration. Monitoring of plasma phenytoin concentration improves dosage adjustments. The usual total plasma phenytoin concentration for optimum response is 0– 20 mg/ L (careful interpretation of total plasma phenytoin concentration is necessary in pregnancy, the elderly, and certain disease states where protein binding may be reduced and it may be more appropriate to measure free plasma phenytoin concentration).
CautionsPatients with acute porphyrias (contraindication).
InteractionsWith AEDs
  • Phenytoin is extensively bound to serum plasma proteins and is prone to competitive displacement. Phenytoin is metabolized by hepatic enzymes (cytochrome P450 CYP2C9 and CYP2C9) and is particularly susceptible to inhibitory drug interactions because it is subject to saturable metabolism.
  • Several AEDs, including eslicarbazepine, oxcarbazepine, topiramate, and valproate, potentially increase phenytoin serum levels.
  • Vigabatrin may decrease phenytoin plasma levels.
  • Carbamazepine, phenobarbital, and valproate may either increase or decrease phenytoin serum levels.
  • Phenytoin is a potent inducer of hepatic drug- metabolizing enzymes and may reduce the levels of drugs metabolized by these enzymes.
  • Phenytoin may alter serum levels and/ or effects of carbamazepine, lamotrigine, phenobarbital, and valproate.

With other drugs
  • Phenytoin serum levels are potentially increased by analgesic/ anti- inflammatory agents (such as azapropazone, phenylbutazone, salicylates), anaesthetics (halothane), antibacterial agents (such as chloramphenicol, erythromycin, isoniazid, sulfadiazine, sulfamethizole, sulfamethoxazoletrimethoprim, sulfaphenazole, sulfisoxazole, sulfonamides), antifungal agents (such as amphotericin b, fluconazole, itraconazole, ketoconazole, miconazole, voriconazole), antineoplastic agents (such as capecitabine, fluorouracil), psychotropic agents (such as chlordiazepoxide, diazepam, disulfiram, fluoxetine, fluvoxamine, methylphenidate, sertraline, trazodone, viloxazine), cardiovascular agents (such as amiodarone, dicoumarol, diltiazem, nifedipine, ticlopidine), H2- antagonists (such as cimetidine), HMG- CoA reductase inhibitors (such as fluvastatin), hormones (such as oestrogens), immunosuppressant drugs (such as tacrolimus), oral hypoglycaemic agents (such as tolbutamide), proton pump inhibitors (such as omeprazole).
  • Phenytoin plasma levels may be decreased by antibacterial agents (such as ciprofloxacin, rifampicin), antineoplastic agents (such as bleomycin, carboplatin, cisplatin, doxorubicin, methotrexate), antiulcer agents (such as sucralfate), antiretrovirals (such as fosamprenavir, nelfinavir, ritonavir), bronchodilators (such as theophylline), cardiovascular agents (such as reserpine), folic acid, hyperglycaemic agents (such as diazoxide), St John抯 wort (Hypericum perforatum).
  • Phenytoin serum levels may be either increased or decreased by antibacterial agents (such as ciprofloxacin), antineoplastic agents, and psychotropic agents (such as chlordiazepoxide, diazepam, and phenothiazines).
  • Phenytoin may alter serum levels and/ or effects of the following drugs: antibacterial agents (such as doxycycline, rifampicin, tetracycline), antifungal agents (such as azoles, posaconazole, voriconazole), antihelminthics (such as albendazole, praziquantel), antineoplastic agents (such as teniposide), antiretrovirals (such as delavirdine, efavirenz, fosamprenavir, indinavir, lopinavir/ ritonavir, nelfinavir, ritonavir, saquinavir), bronchodilators (such as theophylline), cardiovascular agents (such as digitoxin, digoxin, mexiletine, nicardipine, nimodipine, nisoldipine, quinidine, verapamil), coumarin anticoagulants (such as warfarin), ciclosporin, diuretics (such as furosemide), HMG- CoA reductase inhibitors (such as atorvastatin, fluvastatin, simvastatin), hormones (such as oestrogens, oral contraceptives), hyperglycaemic agents (such as diazoxide), immunosuppressant drugs, neuromuscular blocking agents (such as alcuronium, cisatracurium, pancuronium, rocuronium, vecuronium), opioid analgesics (such as methadone), oral hypoglycaemic agents (such as chlorpropamide, glyburide, tolbutamide), psychotropic agents (such as clozapine, paroxetine, quetiapine, sertraline), vitamin D.

With alcohol/food
Acute alcohol intake may increase phenytoin serum levels while chronic alcoholism may decrease serum levels. There are no specific foods that must be excluded from diet when taking phenytoin (phenytoin doses should be taken preferably with or after food).
Special populationsHepatic impairment
Reduce dose to avoid toxicity.

Renal impairment
Nil.

Pregnancy
  • Phenytoin may produce congenital abnormalities in the offspring of a small number of epileptic patients. Therefore, phenytoin should only be used during pregnancy, especially early pregnancy, if in the judgement of the physician the potential benefits clearly outweigh the risk.
  • In addition to the reports of increased incidence of congenital malformations, such as cleft lip/ palate and heart malformations in children of women receiving phenytoin, there have been reports of a foetal hydantoin syndrome, consisting of prenatal growth deficiency, micro- encephaly, and mental deficiency in children born to mothers who have received phenytoin. There have been isolated reports of malignancies, including neuroblastoma, in children whose mothers received phenytoin during pregnancy.
  • ?An increase in seizure frequency during pregnancy occurs in a proportion of patients, possibly due to altered phenytoin absorption or metabolism. Therefore, periodic measurement of serum phenytoin levels is particularly valuable in the management of a pregnant patient with epilepsy as a guide to an appropriate adjustment of dosage; however, postpartum restoration of the original dosage will probably be indicated.
  • Breast- feeding is not recommended for women taking phenytoin because phenytoin appears to be secreted in low concentrations in human milk.
Behavioural and cognitive effects in patients with epilepsyPhenytoin has an overall favourable behavioural profile, although it has been occasionally associated with negative effects on mood and psychotic symptoms (especially at higher doses). The cognitive profile is more problematic, especially in the attention and memory domains. Cognitive adverse effects associated with phenytoin are often dose- dependent and may be particularly obvious in visually guided motor functions.
Psychiatric usePhenytoin has no approved indications in psychiatry, although the results of small randomized studies have shown that it may be useful in the maintenance treatment of bipolar disorder, major depressive disorder, and impulsive aggression.
Chemical Propertieswhite crystals or powder
Chemical PropertiesPhenytoin is a crystalline compound
UsesReduces incidence of grand mal seizures; appears to stabilize excitable membranes perhaps through effects on Na+, K+, and Ca2+ channels.
UsesA sodium channel protein inhibitor
DefinitionChEBI: A imidazolidine-2,4-dione that consists of hydantoin bearing two phenyl substituents at position 5.
Brand nameAnticonvulsant. Dilantin (Pfizer) [Name previously used: Diphenylhydantoin.].
General DescriptionFine white or almost white crystalline powder. Odorless or almost odorless. Tasteless.
Air & Water ReactionsInsoluble in water.
Reactivity Profile5,5-Diphenylhydantoin is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). 5,5-Diphenylhydantoin is incompatible with strong oxidizers and strong bases.
Fire HazardFlash point data for 5,5-Diphenylhydantoin are not available; however, 5,5-Diphenylhydantoin is probably combustible.
Safety ProfileConfirmed carcinogen producing lymphoma, Hodgkin's disease, tumors of the skin and appendages. Experimental carcinogenic and tumorigenic data. A human poison by ingestion. Poison experimentally by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Moderately toxic by an unspecified route. Experimental teratogenic and reproductive effects. Human systemic effects by ingestion: dermatitis, change in motor activity (specific assay), ataxia (loss of muscle coordmation), degenerative brain changes, encephalitis, hallucinations, dtstorted perceptions, irritabihty, and jaundice. Human teratogenic effects by ingestion: developmental abnormalities of the central nervous system, carlovascular (circulatory) system, musculoskeletal system, craniofacial area, skin and skin appendages, eye, ear, other developmental abnormalities. Effects on newborn include abnormal growth statistics (e.g., reduced weight gain), physical abnormakties, other postnatal measures or effects, and delayed effects. Human mutation data reported. A drug for the treatment of grand mal and psychomotor seizures. When heated to decomposition it emits toxic fumes of NOx
Potential ExposurePhenytoin is an amide pharmaceutical used in the treatment of grand mal epilepsy, Parkinson’s syndrome; and in veterinary medicine. Human exposure to phenytoin occurs principally during its use as a drug. Figures on the number of patients using phenytoin are not available, but phenytoin is given to a major segment of those individuals with epilepsy. The oral dose rate is initially 100 mg given 3 times per day and can gradually increase by 100 mg every 24 weeks until the desired therapeutic response is obtained. The intravenous dose is 200350 mg/day.
First aidSkin Contact: Flood all areas of body that have contacted the substance with water. Don’t wait to remove contaminated clothing; do it under the water stream. Use soap to help assure removal. Isolate contaminated clothing when removed to prevent contact by others. Eye Contact: Remove any contact lenses at once. Flush eyes well with copious quantities of water or normal saline for at least 2030 minutes. Seek medical attention. Inhalation: Leave contaminated area immediately; breathe fresh air. Proper respiratory protection must be supplied to any rescuers. If coughing, difficult breathing or any other symptoms develop, seek medical attention at once, even if symptoms develop many hours after exposure. Ingestion: If convulsions are not present, give a glass or two of water or milk to dilute the substance. Assure that the person’s airway is unobstructed and contact a hospital or poison center immediately for advice on whether or not to induce vomiting.
ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification MethodsCrystallise the hydantoin from EtOH. [Beilstein 24 III/IV 1748.]
IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Similar organic amides react with azo and diazo compounds, releasing toxic gases. Contact with reducing agents can release flammable gases. Amides are very weak bases but they can react as acids, forming salts. Mixing amides with dehydrating agents such as phosphorus pentoxide or thionyl chloride generates the corresponding nitrile.
5,5-Diphenylhydantoin Preparation Products And Raw materials
Preparation Products2,4,6-Trifluorophenol
Raw materialsBenzaldehyde
Tag:5,5-Diphenylhydantoin(57-41-0) Related Product Information
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